N-(3-Nitro­benzyl­idene)-p-toluidine

The title compound, C₁₄H₁₂N₂O₂, is non-planar. The dihedral angle between the two benzene rings is 32.1 (2)° and the nitro group is at an angle of 13.2 (2)° with respect to its attached benzene ring. In the crystal structure, the mol­ecules are stacked through π–π inter­actions. The stacks are arranged through π–π and C—H...π inter­actions, forming chains along [001], which are further connected by C—H...O and C—H...N hydrogen bonds, forming networks along [100]. The networks are connected by C—H...O hydrogen bonds along [010].

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.084
• Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1C    ..  O2      ..       2.81 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  O1      ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  N1      ..       2.82 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O2      ..       2.68 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C3     ..  O1      ..       3.78 Ang.

Alert level G
ABSTY01_ALERT_1_G  Extra text has been found in the _exptl_absorpt_correction_type
            field, which should be only a single keyword. A literature
            citation should be included in the _exptl_absorpt_process_details
            field.
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.00
           From the CIF: _reflns_number_total               1629
           Count of symmetry unique reflns         1629
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1990); cell refinement: XSCANS (Siemens, 1990); data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-[(3-nitrophenyl)methylene]-4-methylbenzenamine N-(4-methylphenyl)-3-nitrobenzylideneamine

Crystal data

C14H12N2O2	Dx = 1.277 Mg m^−3
Mr = 240.26	Melting point = 368–369 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2c-2ac	Cell parameters from 23 reflections
a = 13.413 (2) Å	θ = 3.0–15.8°
b = 13.115 (2) Å	µ = 0.09 mm^−1
c = 7.104 (1) Å	T = 291 K
V = 1249.7 (3) Å^3	Granular, white–yellow
Z = 4	0.56 × 0.52 × 0.40 mm
F(000) = 504

Data collection

Siemens P4 diffractometer	1086 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.008
Graphite monochromator	θmax = 28.0°, θmin = 1.6°
ω scans	h = −1→17
Absorption correction: ψ scans (XSCANS; Siemens, 1990)	k = −17→0
Tmin = 0.950, Tmax = 0.970	l = 0→9
1953 measured reflections	3 standard reflections every 97 reflections
1629 independent reflections	intensity decay: 3.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0451P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
1629 reflections	Δρmax = 0.13 e Å^−3
165 parameters	Δρmin = −0.12 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (2)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.77127 (13)	−0.27624 (12)	0.2682 (4)	0.0951 (8)
O2	0.88585 (12)	−0.17832 (12)	0.3707 (3)	0.0892 (7)
N1	0.81445 (12)	0.18752 (12)	0.4738 (3)	0.0537 (5)
N2	0.79924 (14)	−0.19580 (14)	0.3337 (3)	0.0631 (6)
C1	0.9508 (2)	0.59089 (16)	0.6447 (5)	0.0865 (9)
H1A	1.0200	0.5960	0.6111	0.104*
H1B	0.9434	0.6029	0.7773	0.104*
H1C	0.9132	0.6407	0.5758	0.104*
C2	0.91301 (18)	0.48545 (16)	0.5975 (4)	0.0611 (6)
C3	0.82443 (18)	0.47073 (16)	0.5014 (4)	0.0641 (7)
H3	0.7872	0.5272	0.4649	0.077*
C4	0.79013 (16)	0.37472 (14)	0.4585 (4)	0.0583 (6)
H4	0.7305	0.3670	0.3931	0.070*
C5	0.84409 (15)	0.28933 (15)	0.5123 (3)	0.0505 (5)
C6	0.93294 (15)	0.30283 (16)	0.6048 (4)	0.0564 (6)
H6	0.9708	0.2464	0.6389	0.068*
C7	0.96659 (17)	0.39984 (15)	0.6479 (4)	0.0615 (6)
H7	1.0266	0.4075	0.7120	0.074*
C8	0.72335 (15)	0.16318 (16)	0.4758 (4)	0.0549 (6)
H8	0.6759	0.2128	0.5030	0.066*
C9	0.69046 (14)	0.05874 (15)	0.4363 (3)	0.0527 (5)
C10	0.58959 (15)	0.03421 (18)	0.4323 (5)	0.0717 (8)
H10	0.5424	0.0847	0.4545	0.086*
C11	0.55881 (17)	−0.06425 (19)	0.3958 (5)	0.0836 (9)
H11	0.4911	−0.0794	0.3934	0.100*
C12	0.62642 (17)	−0.13928 (18)	0.3632 (4)	0.0687 (7)
H12	0.6057	−0.2056	0.3383	0.082*
C13	0.72580 (14)	−0.11518 (14)	0.3680 (3)	0.0518 (5)
C14	0.75947 (16)	−0.01843 (13)	0.4046 (3)	0.0502 (5)
H14	0.8275	−0.0047	0.4082	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0914 (15)	0.0614 (9)	0.132 (2)	−0.0033 (9)	−0.0029 (14)	−0.0254 (13)
O2	0.0554 (10)	0.0763 (11)	0.136 (2)	0.0044 (8)	0.0072 (12)	−0.0206 (13)
N1	0.0569 (11)	0.0501 (10)	0.0541 (12)	0.0051 (8)	−0.0040 (10)	0.0039 (9)
N2	0.0623 (11)	0.0591 (11)	0.0680 (16)	−0.0013 (10)	0.0078 (11)	−0.0033 (11)
C1	0.118 (2)	0.0587 (15)	0.083 (2)	0.0019 (14)	−0.021 (2)	−0.0101 (15)
C2	0.0785 (15)	0.0513 (12)	0.0537 (14)	0.0047 (11)	−0.0037 (14)	−0.0066 (12)
C3	0.0781 (15)	0.0543 (13)	0.0599 (15)	0.0139 (11)	−0.0119 (14)	0.0061 (12)
C4	0.0615 (12)	0.0552 (12)	0.0583 (15)	0.0063 (10)	−0.0090 (12)	0.0066 (13)
C5	0.0553 (12)	0.0484 (11)	0.0479 (14)	0.0062 (10)	0.0008 (11)	−0.0005 (10)
C6	0.0562 (12)	0.0546 (12)	0.0583 (15)	0.0110 (10)	−0.0056 (12)	−0.0012 (12)
C7	0.0617 (13)	0.0636 (15)	0.0593 (15)	0.0029 (11)	−0.0107 (12)	−0.0062 (13)
C8	0.0532 (13)	0.0566 (12)	0.0549 (14)	0.0099 (9)	0.0019 (12)	0.0040 (11)
C9	0.0505 (11)	0.0568 (12)	0.0510 (13)	−0.0006 (9)	−0.0010 (11)	0.0099 (11)
C10	0.0481 (12)	0.0697 (15)	0.097 (2)	0.0086 (10)	0.0008 (14)	0.0143 (16)
C11	0.0475 (12)	0.0775 (16)	0.126 (3)	−0.0088 (12)	−0.0008 (15)	0.013 (2)
C12	0.0535 (13)	0.0617 (13)	0.0908 (19)	−0.0090 (11)	−0.0025 (14)	0.0086 (15)
C13	0.0498 (12)	0.0554 (12)	0.0501 (12)	−0.0001 (9)	0.0020 (11)	0.0057 (11)
C14	0.0427 (9)	0.0584 (11)	0.0494 (12)	−0.0027 (10)	0.0009 (10)	0.0044 (10)

Geometric parameters (Å, º)

O1—N2	1.213 (2)	C6—C7	1.384 (3)
O2—N2	1.213 (2)	C6—H6	0.9300
N1—C8	1.263 (2)	C7—H7	0.9300
N1—C5	1.420 (3)	C8—C9	1.466 (3)
N2—C13	1.466 (3)	C8—H8	0.9300
C1—C2	1.511 (3)	C9—C14	1.390 (3)
C1—H1A	0.9600	C9—C10	1.391 (3)
C1—H1B	0.9600	C10—C11	1.380 (3)
C1—H1C	0.9600	C10—H10	0.9300
C2—C7	1.380 (3)	C11—C12	1.358 (3)
C2—C3	1.384 (3)	C11—H11	0.9300
C3—C4	1.375 (3)	C12—C13	1.370 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.387 (3)	C13—C14	1.372 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.372 (3)
C8—N1—C5	120.42 (18)	C2—C7—C6	121.4 (2)
O1—N2—O2	123.0 (2)	C2—C7—H7	119.3
O1—N2—C13	118.92 (19)	C6—C7—H7	119.3
O2—N2—C13	118.13 (18)	N1—C8—C9	121.67 (19)
C2—C1—H1A	109.5	N1—C8—H8	119.2
C2—C1—H1B	109.5	C9—C8—H8	119.2
H1A—C1—H1B	109.5	C14—C9—C10	118.42 (19)
C2—C1—H1C	109.5	C14—C9—C8	120.73 (17)
H1A—C1—H1C	109.5	C10—C9—C8	120.84 (19)
H1B—C1—H1C	109.5	C11—C10—C9	120.7 (2)
C7—C2—C3	117.5 (2)	C11—C10—H10	119.6
C7—C2—C1	120.8 (2)	C9—C10—H10	119.6
C3—C2—C1	121.7 (2)	C12—C11—C10	120.7 (2)
C4—C3—C2	121.6 (2)	C12—C11—H11	119.7
C4—C3—H3	119.2	C10—C11—H11	119.7
C2—C3—H3	119.2	C11—C12—C13	118.6 (2)
C3—C4—C5	120.2 (2)	C11—C12—H12	120.7
C3—C4—H4	119.9	C13—C12—H12	120.7
C5—C4—H4	119.9	C12—C13—C14	122.6 (2)
C6—C5—C4	118.76 (19)	C12—C13—N2	118.90 (19)
C6—C5—N1	117.18 (18)	C14—C13—N2	118.53 (17)
C4—C5—N1	124.04 (19)	C13—C14—C9	119.02 (19)
C5—C6—C7	120.5 (2)	C13—C14—H14	120.5
C5—C6—H6	119.8	C9—C14—H14	120.5
C7—C6—H6	119.8
C7—C2—C3—C4	0.5 (4)	C14—C9—C10—C11	−0.7 (4)
C1—C2—C3—C4	180.0 (3)	C8—C9—C10—C11	−179.8 (3)
C2—C3—C4—C5	0.4 (4)	C9—C10—C11—C12	0.1 (5)
C3—C4—C5—C6	−1.5 (3)	C10—C11—C12—C13	0.2 (4)
C3—C4—C5—N1	−179.9 (2)	C11—C12—C13—C14	0.1 (4)
C8—N1—C5—C6	146.0 (2)	C11—C12—C13—N2	179.8 (3)
C8—N1—C5—C4	−35.6 (3)	O1—N2—C13—C12	13.6 (4)
C4—C5—C6—C7	1.7 (3)	O2—N2—C13—C12	−167.1 (2)
N1—C5—C6—C7	−179.8 (2)	O1—N2—C13—C14	−166.7 (2)
C3—C2—C7—C6	−0.3 (4)	O2—N2—C13—C14	12.5 (3)
C1—C2—C7—C6	−179.8 (3)	C12—C13—C14—C9	−0.7 (4)
C5—C6—C7—C2	−0.8 (4)	N2—C13—C14—C9	179.6 (2)
C5—N1—C8—C9	179.9 (2)	C10—C9—C14—C13	0.9 (4)
N1—C8—C9—C14	3.3 (4)	C8—C9—C14—C13	−180.0 (2)
N1—C8—C9—C10	−177.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1^i—H1C^i···O2	0.96	2.81	3.703 (3)	155
C3^i—H3^i···O1	0.93	2.94	3.777 (2)	150
C10^ii—H10^ii···O2	0.93	2.50	3.351 (3)	152
C11^ii—H11^ii···N1	0.93	2.82	3.696 (3)	158
C6^iii—H6^iii···O2	0.93	2.68	3.485 (3)	145

Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y, z; (iii) −x+2, −y, z−1/2.